Biggest Sports Betting Wins — Saturday, May 16, 2026
5 notable wins | Total payouts: $311,980 | Total taxes: $88,044
5-leg SGP on Elite 8 Matchup — $500 turned into $131,500
Source: RedditOBBBA Note: If this bettor had $131,000 in losses elsewhere, they'd still owe $3,144 in 'phantom income' tax under 2026 OBBBA rules.
9-leg parlay on Rangers vs Bruins — $50 turned into $109,400
Source: X/TwitterOBBBA Note: If this bettor had $109,350 in losses elsewhere, they'd still owe $2,624 in 'phantom income' tax under 2026 OBBBA rules.
futures bet on Astros vs Rangers — $200 turned into $59,000
Source: RedditOBBBA Note: If this bettor had $58,800 in losses elsewhere, they'd still owe $1,411 in 'phantom income' tax under 2026 OBBBA rules.
8-leg parlay on Main Card Opener — $10 turned into $11,940
Source: X/TwitterOBBBA Note: If this bettor had $11,930 in losses elsewhere, they'd still owe $286 in 'phantom income' tax under 2026 OBBBA rules.
moneyline bet on 49ers vs Rams — $20 turned into $140
Source: Reddit